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"How do I keep from shocking a team member when we need to have a hard talk they donโ€™t see coming?"

difficult conversations team conflict May 18, 2023
team members having a tough conversation

Somedays, leadership is just hard.

The new project manager doesn’t have the skillset to do the job. Your assistant is careless with details and hurting your personal brand as a leader. Or maybe you’ve learned some news about someone on your team sexually harassing another person.

Difficult conversations are just are part of the job for a leader. And as an enneagram 9w8, I spent years trying to figure out my style when it came to leading difficult conversations. 

One of the things I started doing a few years back that really seems to work for me is how I start a difficult conversation meeting. (Pro Tip: The first thing I learned is to make sure anyone in the meeting is there early. There is nothing more awkward than trying to fake small talk with the recipient of your difficult conversation while you wait on someone who is late to the meeting.) But the thing I started doing was just beginning the conversation by leveling with them that this is a hard conversation for you and it will be for them.

Let it hang there a second after you say it. Let everyone take a deep breath and emotionally prepare for what’s about to take place. Calling it what it is seems to take a little of the surprise out of the conversation to come. 

In some cases, I even started giving the person a heads up before the meeting. It might be a text or email that says, “Hey Brad. In our 3:00 mtg today, I want to talk about how things are going since our last check-in. I’m worried that the project is getting away from us. I just wanted to give you a heads up so you won’t feel ambushed. See you in a little bit.”

The heads up just avoids the shock they may feel if they really have no idea why you’ve asked for the meeting. And they most likely know you need to talk about whatever it is. It lets them prep themselves emotionally to have an honest conversation and level with you about the best options. 

Hard conversations can still be kind and personable. We are, after all, still trying to solve the same problems and help each other. This just gives them an extra moment to decide how they’ll react and be intentional.

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